Copper-catalyzed radical trans-selective hydroboration of ynamides with N-heterocyclic carbene boranes

Summary: Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical trans-hydroboration of ynamides with N-heterocyclic carbene (NHC)-ligated borane is reported, which leads to a...

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Bibliographic Details
Main Authors: Kefeng Wang, Qingzhen Yu, Wenli Mao, Yuxin Zheng, Jing Xu, Yukun Wang
Format: Article
Language:English
Published: Elsevier 2022-09-01
Series:iScience
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2589004222012494
Description
Summary:Summary: Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical trans-hydroboration of ynamides with N-heterocyclic carbene (NHC)-ligated borane is reported, which leads to a series of trans-boryl enmides that can be conveniently transformed into various multi-substituted enamides. Further investigation showcased that our method is robust and scalable. The mechanism of this unique reaction is studied and discussed.
ISSN:2589-0042